Acetic Acid → HCID 178492203, compound

HRID 511007Notes

Reaction equation

[Cl:1][C:2]1[C:3]([F:30])=[C:4]([C:7]([O:28][CH3:29])=[C:8]([CH:10]([NH:12][C:13]2[N:21]=[CH:20][N:19]=[C:18]3[C:14]=2[N:15]=[CH:16][N:17]3C2CCCCO2)[CH3:11])[CH:9]=1)[CH:5]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[NH:49]1[CH2:54][CH2:53][O:52][CH2:51][CH2:50]1.C([BH3-])#N.[Na+].FC(F)(F)C(O)=O.C1COCC1.Cl.O>C1COCC1>[Cl:1][C:2]1[C:3]([F:30])=[C:4]([CH2:5][N:49]2[CH2:54][CH2:53][O:52][CH2:51][CH2:50]2)[C:7]([O:28][CH3:29])=[C:8]([CH:10]([NH:12][C:13]2[N:21]=[CH:20][N:19]=[C:18]3[C:14]=2[N:15]=[CH:16][NH:17]3)[CH3:11])[CH:9]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 3-chloro-2-fluoro-6-methoxy-5-(1-{[9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl]amino}ethyl)benzaldehyde (10 mg, 0.023 mmol), in THF (0.95 mL) was stirred at 40° C. for 1 hour. Sodium triacetoxyborohydride (15 mg, 0.069 mmol) and acetic acid (50 μL, 0.88 mmol) were added and the mixture was stirred at 40° C. overnight. Morpholine (20 μL, 0.23 mmol) and sodium cyanoborohydride (14 mg, 0.23 mmol) were added and the mixture was heated at 40° C. for 1 hour. The solvents were stripped down and few drops of trifluoroacetic acid/THF solution (1:1) were added and the mixture stirred for 30 minutes. The mixture was treated with 6.0 M HCl in water (0.5 mL, 3 mmol) for 30 minutes. Purification by preparative LCMS (pH 10) gave the desired compound (3.4 mg, 35%). LCMS calculated for C19H23ClFN6O2 (M+H)+: m/z=421.2. found: 421.1. 1H NMR (DMSO-d6, 500 MHz) δ 12.91 (1H, br s), 8.17 (2H, m), 7.72 (1H, m), 5.89 (1H, br s), 4.05 (3H, s), 3.50 (7H, m), 2.41 (4H, m), 1.42 (3H, m).

Workup

temperaturethe mixture was heated at 40° C. for 1 hour
stirringthe mixture stirred for 30 minutes
customPurification by preparative LCMS (pH 10)

Sources & evidence

ORD record: ord-95ffa973034a466d83a9a78b5170f2b7
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096600B2

Reaction notes

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